9. Hank Williams Jr.
Most of Hank Williams Jr.'s early days were spent in the shadow of his legendary father, Hank Williams (more on him later). Style-wise, this wasn't necessarily a bad thing. Junior looked great in the '60s, but wanted to forge his own path. After finding drugs, alcohol, and a Southern rock influence, his music became known in its own right, and he definitely stopped dressing like his Pops.
After a brutal mountain climbing accident in 1975, Hank grew a beard and wore sunglasses and a cowboy hat to cover up his scars and disfigurements. The look soon became his signature style, and co-incided with his rise to superstardom. Now you know him as that guy you heard every Monday night until he made some seriously controversial comments.